3-Chloro-2-methyl-1-propene → HCID 24707938, compound

HRID 928653Notes

Reaction equation

HRID 928653 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]([CH3:11])=[CH2:10].[Br:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20]>CN(C=O)C>[Br:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[O:20][CH2:8][C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 24707938HCID 24707938, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (829 mg, 6.00 mmol) and 3-chloro-2-methyl-1-propene (0.591 mL, 6.00 mmol) were added to a solution (25 mL) of 2-bromo-4-fluorophenol (955 mg, 5.00 mmol) in DMF, and stirred at 60° C. overnight. The solvent was distilled away under reduced pressure, and after diluted with ethyl acetate, the resultant was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away, and the resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. additionafter diluted with ethyl acetate
  3. washthe resultant was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away
  6. customthe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a5486198472f44b29902907190704614
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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